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Volume 14, Issue 1
Displaying 1-20 of 20 articles from this issue
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Masuo Akagi, Isamu Aoki, Takayoshi Uematsu1966 Volume 14 Issue 1 Pages 1-9
Published: January 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1. The metabolic fate of p-ethoxyphenylurea in the rabbit was studied. 2. About 40% of the dose was excreted as phenolic substances, presumably p-hydroxyphenylurea. The phenolic products were excreted as the unconjugated (7%), glucuronide (11%), and sulfate (23% of p-ethoxyphenylurea fed). p-Hydroxyphenylurea was isolated as its diacetyl dericative. The sulfate and glucuronide of p-hydroxyphenylurea were detected. 3. It was suggested that the main glucuronide of p-ethoxyphenylurea was N-glucuronide. This compound accounted for about 27% of p-ethoxyphenylurea fed. The N-glucuronide was isolated as crystals of both potassium and ammonium salts of p-ethoxyphenylurea N-glucuronide. 4. About 3% of the dose was excreted unchanged.View full abstractDownload PDF (1017K) -
Masuo Akagi, Isamu Aoki, Takayoshi Uematsu, Takashi Iyanagi1966 Volume 14 Issue 1 Pages 10-14
Published: January 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN-Glucosiduronates of arylureas excreted in the rabbit urine dosed with arylureas were isolated and confirmed to be identical with ammonium 1-[3-(aryl) ureido]-1-deoxy-D-glucopyranosiduronates which were synthesized from glucuronic acid and arylureas in pyridine. It is suggested that N-glucosiduronate conjugation is a general pathway of arylurea metabolism in the rabbit.View full abstractDownload PDF (730K) -
Masuo Akagi, Isamu Aoki, Masanobu Haga, Takayoshi Uematsu, Masakatsu S ...1966 Volume 14 Issue 1 Pages 14-18
Published: January 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to determine the structure of p-ethoxyphenylurea N-glucuronide isolated from the rabbit urine dosed with p-ethoxyphenylurea, ammonium and potassium 1-[3-(p-ethoxyphenyl) ureido]-1-deoxy-β-D-glucopyranuronates were synthesized from 2, 3, 4, 6-tetra-O-acetyl-β-D-glucopyranosylisocyanate, isothiocyanate, or methyl 1-[3-(p-ethoxyphenyl) thioureido]-1-deoxy-β-D-glucopyranuronate as starting materials, and were identical with the N-glucuronides from the rabbit urine.View full abstractDownload PDF (651K) -
Masuo Akagi, Isamu Aoki, Takayoshi Uematsu, Takashi Iyanagi1966 Volume 14 Issue 1 Pages 18-21
Published: January 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1-[3-(Aryl) ureido]-1-deoxy-D-glucofuranuronolactones were synthesized from arylureas and glucuronolactone. Some of them were converted to ammonium 1-[3-(aryl)-ureido]-1-deoxy-β-D-glucopyranuronates by treatment with alkaline, which were identical with metabolites from the rabbit urine dosed with the corresponding arylureas.View full abstractDownload PDF (565K) -
Seigo Ueda1966 Volume 14 Issue 1 Pages 22-29
Published: January 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe interactions between eight water insoluble substances and sodium benzoate derivatives in aqueous solutions were studied spectrophotometrically. It was found that the water insoluble substance used formed one to one molecular complex with sodium benzoate derivative in aqueous system. The formation constants of the complexes were determined at 25° and 60°, with which the enthalpy change ΔH and the entropy change ΔS of complex formation were obtained. As a result, it was suggested that the driving force of the complex formation would be due to charge transfer force or hydrogen bonding.View full abstractDownload PDF (656K) -
Seigo Ueda1966 Volume 14 Issue 1 Pages 29-38
Published: January 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe solubilities of the eight water insoluble substances in aqueous sodium benzoates solutions were determined. As a result of these measurement, it was found that any water insoluble substances were solubilized by sodium benzoate derivatives. Using the formation constants of the complexes, which were obtained by spectrophotometric measurements, the amounts of the complex in the water insoluble substance solubilized by sodium benzoate could be obtained. These amounts were found to be rather smaller than the solubility increase of the water insoluble substances. So, it was concluded that the other factor than complex formation should be considered as the mechanism of solubilization by sodium benzoate derivatives.View full abstractDownload PDF (805K) -
Seigo Ueda1966 Volume 14 Issue 1 Pages 39-45
Published: January 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn the previous reports, it was suggested that as the mechanism of the solubilization by sodium benzoate derivatives, another factor than complex formation. between solubilizing and solubilized molecules had to be considered. In this paper, it was proved that the activity coefficients of water insoluble substances in aqueous solutions decreased by addition of sodium benzoate derivatives. It was concluded that the mechanism of the solubilization by sodium benzoate derivatives composed of the two main factors, one of which was complex formation between solubilizied and solubilizing molecules and the other of which was the salting in effect of sodium benzoate derivatives.View full abstractDownload PDF (725K) -
Morio Ikehara, Kei Muneyama1966 Volume 14 Issue 1 Pages 46-49
Published: January 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSStarting from 8-bromoguanosine, 8-methylsulfonylguanosine, 8-dimthylaminoguanosine and 8-methoxyguanosine were synthesized. The reaction of 8-methylsulfonylguanosine with acid, alkali and t-butoxide were investigated. In the former two cases cleavage of nucleoside linkage was observed. In the latter case cleavage of pyrimidine ring probably occurred.View full abstractDownload PDF (563K) -
Michiya Kimura, Masahiko Tohma, Itsuo Yoshizawa1966 Volume 14 Issue 1 Pages 50-55
Published: January 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree kinds of new steroidsaponin, convallasaponin-A, m.p. 238∼240° (decomp.), [α]22D-39.7°(CHCl3), convallasaponin-B, m.p.273∼274°, [α]22D-55.7°(CHCl3-MeOH), and convallasaponin-C, m.p.218∼221°(decomp.), [α]19D-89.7°(CHCl3-MeOH) were isolated from the flowers of Convallaria keisukei MIQ., Japanese lily of the valley. Upon hydrolysis convallasaponin-A and -B gave new steroidsapogenins, convallagenin-A, m.p.268∼269°, [α]20D-28.0°(CHCl3-MeOH) and convallagenin-B, m.p.277∼278°, [α]21D-42.7°(CHCl3-MeOH) respectively, together with L-arabinose as the sugar moiety. Convallasaponin-C afforded isorhodeasapogenin, L-arabinose and L-rhamnose. It is likely that convallagenin-A and -B belong to tri- and tetrahydroxy-25L-steroidsapogenin respectively, having one unacetylable hydroxyl group in each molecule.View full abstractDownload PDF (785K) -
Michiya Kimura, Masahiko Tohma, Itsuo Yoshizawa1966 Volume 14 Issue 1 Pages 55-61
Published: January 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSConvallasaponin-C (I) from Convallaria keisukei MIQ. was completely hydrolyzed affording isorhodeasapogenin (25D-5β-spirostane-1β, 3β-diol), L-arabinose and L-rhamnose. The molar ratio of these sugars was found to be 1 : 2 on the basis of separating their tetraazoates prepared from the sugar moiety obtained after hydrolysis. This ratio was also indicated by gas chromatography (Fig.1). Prosapogenin-I and prosapogenin-II were obtained by the partial hydrolysis of I. The former was further hydrolyzed into isorhodeasapogenin and L-arabinose which were also obtained with the additional sugar component, L-rhamnose, from prosapogenin-II. Hydrolysis of the permethylate (II), fully methylated I, afforded isorhodeasapogenin monomethylate (III) which was oxidized to C3-keto derivative (IV) by chromium trioxide in acetic acid. Hydrolysis of II afforded three partially methylated sugars, 3, 4-di-O-methyl-L-arabopyranose, 2, 4-di-O-methyl-L-rhamnopyranose and 2, 3, 4-tri-O-methyl-L-rhamnopyranose in a molar ratio of 1 : 1 : 1(Fig.4). Analysis of the molecular rotation differences (Table IV) between isorhodeasapogenin, prosapogenin-I, -II and I would indicate that the glycosidic linkages in these substances are all in the α-form. Consequently the structure of convallasaponin-C might reasonably be formulated as isorhodeasapogenin (3)α-L-rhamnopyranosyl (1→3 rham.)-α-L-rhamnopyranosyl (1→2 arab.)-α-L-arabopyranoside (Chart 2).View full abstractDownload PDF (809K) -
Hidetoshi Yoshimura, Kazuta Oguri, Hisao Tsukamoto1966 Volume 14 Issue 1 Pages 62-67
Published: January 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA simple and sensitive method for extraction and detection of morphine in urine was described. The continuous extraction method showed a virtually complete recovery of morphine and preventecd the formation of emulsion unavoidable in the extraction by shaking. The hydrolysis condition which led to liberation of most of morphine from the conjugates in urine was found to be that of heating for 30 minutes, in the 15% hydrochloric acid concentration. This procedure was simple, but afforded the comparable result to that of sealed tube hydrolysis in the 5% hydrochloric acid concentration. Double thin-layer chromatographic method was successfully applied first to the separation of morphine from a large amount of impurtities in the urine extract using thicker plate (1mm.) and then to the final detection of morphine using ordinary one (0.25mm.).View full abstractDownload PDF (743K) -
Tetsuji Kametani, Seiichi Takano, Kazuko Masuko, Fujinori Sasaki1966 Volume 14 Issue 1 Pages 67-72
Published: January 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDiastereoisomeric mixture of O, O-dibenzyl-liensinine (II) was successfully obtained by the modified Ullmann reaction of dl-1-(4-benzyloxybenzyl)-2-methyl-6-methoxy-7-hydrozy-1, 2, 3, 4-tetrahydroisoquinoline (XVII) with dl-1-(3-bromo-4-benzyloxybenzyl)-2-methyl-6, 7-dimethoxy-1, 2, 3, 4-tetrahydroisoquinoline (X) which has a large substituent such as benzyloxy-group at the ortho position of bromobenzene nucleus, without any detectable side reaction on the thin-layer chromatography. Removal of benzyl group by treating II with hydrochloric acid gave diastereoisomeric mixture of liensinine (I'), whose infrared and ultraviolet spectra were identical with those of natural product.View full abstractDownload PDF (752K) -
Tetsuji Kametani, Seiichi Takano, Ryobun Yanase, Chihiro Kibayashi, Hi ...1966 Volume 14 Issue 1 Pages 73-77
Published: January 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe diamide (X) was prepared from 3, 4-dimethoxyphenethylamine and acid chloride (IX). This compound (X) was also obtained by condensation of dimethyl 4-benzyloxy-3, 4'-oxydiphenyldiacetate (VIIb) with the above amine. Cyclization of the diamide (X), followed by the reduction of the methiodide of XI, gave the stereoisomeric mixture of O-benzyldauricine (III), which was also obtained by Ullmann reaction of XIII with XIV.View full abstractDownload PDF (672K) -
Tetsuji Kametani, Haruhiko Yagi1966 Volume 14 Issue 1 Pages 78-82
Published: January 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe diamide (IX) was prepared from the 2, 4'-oxy-4, 5-bisbenzyloxydibenzoic acid (VII) and 3-methoxy-4-benzyloxyphenethylamine by Arndt-Eistert reaction. Cyclization of IX gave the dihydroisoquinoline (X); reduction of the dimethiodide (XI) with sodium borohydride, followed by hydrolysis with concentrated hydrochloric acid-ethanol (1 : 1), gave the stereoisomeric mixture of magnolamine (I).View full abstractDownload PDF (720K) -
Shigeru Takanashi, Yoshinobu Hirasaka, Minoru Kawada, Morizo Ishidate1966 Volume 14 Issue 1 Pages 82-86
Published: January 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHyalobiuronic acid, the unit disaccharide of hyaluronic acid, and chondrosine, that of chondroitin sulfuric acid A or C, were synthesized by condensing corresponding aminosugar derivatives with acetobromo derivative of glucuronic acid by the Koenigs-Knorr reaction.View full abstractDownload PDF (678K) -
Kenzo Sirakawa, Osami Aki, Susumu Tsushima, Kazuo Konishi1966 Volume 14 Issue 1 Pages 89-91
Published: January 25, 1966
Released on J-STAGE: March 31, 2008
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Yukichi Kishida, Tetsuo Hiraoka, Junya Ide, Atsusuke Terada, Norio Nak ...1966 Volume 14 Issue 1 Pages 92-94
Published: January 25, 1966
Released on J-STAGE: March 31, 2008
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Kiyoshi Hata, Mitsugi Kozawa, Yasumasa Ikeshiro1966 Volume 14 Issue 1 Pages 94-96
Published: January 25, 1966
Released on J-STAGE: March 31, 2008
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Mikio Yamazaki, Shoji Shibata1966 Volume 14 Issue 1 Pages 96-97
Published: January 25, 1966
Released on J-STAGE: March 31, 2008
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Kazumitsu Nishimoto, Miyoko Ito, Shinsaku Natori, Taichi Ohmoto1966 Volume 14 Issue 1 Pages 97-99
Published: January 25, 1966
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (409K)
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